Sulfur → HCID 88214287, compound

HRID 2269307Notes

Reaction equation

HRID 2269307 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[C:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:20][CH:19]=1)[O:16][CH3:17].[S]>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@@H:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:20][CH:19]=1)[O:16][CH3:17]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 88215764HCID 88215764, compound

Product 1

HCID 88214287HCID 88214287, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 17 (640 mg, 1.5 mmol) was dissolved in THF (50 mL) and hydrogenated in the presence of sulfur-resistant 10% palladium on carbon (640 mg) on a Parr Shaker at 50 PSI for 20 hours. The catalyst was removed via filtration through diatomaceous earth and the filtrate was concentrated in vacuo. The residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1) plus 5% acetic acid, to afford crude material which was further purified by (dissolving the residue in 50 mL of ethyl acetate, washing with water (25 mL), saturated aqueous sodium bicarbonate (25 mL), brine (25 mL) and drying (MgSO4), to afford a colorless gum (229 mg, 35%). 1HNMR (300 MHz, CDCl3): δ2.0 (m, 2H), 2.3 (s, 3H), 2.5 (t, 2H), 3.1 (dd, 1H), 3.2 (s, 3H), 3.5 (dd, 1H), 4.1 (dd, 1H), 4.4 (dd, 1H), 7.2 (m, 4H), 7.4 (m, 3H), 7.9 (m, 2H), 8.1 (bs, 1H, NH).

Workup

  1. customThe catalyst was removed via filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified on silica gel
  4. washeluting with hexane/ethyl acetate (3/1) plus 5% acetic acid
  5. customto afford crude material which
  6. customwas further purified by (
  7. dissolutiondissolving the residue in 50 mL of ethyl acetate
  8. washwashing with water (25 mL), saturated aqueous sodium bicarbonate (25 mL), brine (25 mL)
  9. dry with materialdrying (MgSO4)

Sources & evidence

ORD record
ord-4b3b75f3c0404fc49bec5eeccbd7c3e1
Source dataset
uspto-grants-2001_12
Patent number
US06329408B1

Reaction notes

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